Synthesis of a novel class of fatty acids-derived isoquinolines

Two series of novel tetrahydroisoquinoline derivatives bearing at C-1 position a carbon chain derived from fatty acids were prepared employing two complementary synthetic methodologies. The Pictet–Spengler condensation was performed on myristyl, palmityl, stearyl and oleyl aldehydes, whereas the Bischler–Napieralski cyclization used pelargonic, stearic, linolenic and arachidonic acids. The ability to apply both methods allows further labeling of the final 1-substituted-1,2,3,4-tetrahydroisoquinolines for biological studies.